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A past exam from whittier college's organic chemistry course, chem 231a. The exam covers various topics including conformational isomers, organometallic reagents, oxidation reactions, and reaction mechanisms. Students are required to answer multiple-choice questions, predict major products, and provide reagents for given transformations.
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Name: Whittier College
120 Points Total November 24, 2003
1a. What is a conformational isomer? Provide two structures that are conformational isomers and explain their relationship.
1b. What is an organometallic reagent? Provide an example and use this example to explain its reactivity.
1c. What kind of reaction do organic chemists consider to be an oxidation reaction? Provide an example and explain briefly.
1d. What is the 3-D shape of a cyclohexane? Why is it this shape?
2a.
2b.
Na 2 Cr 2 O 7
OH
O
Cl
OH
Mg / Et 2 O
Aqueous Work-up
O H
2c.
O
O O
H (^) Li
O (THF)
Br
5a.
5b.
Compound A
OH CF 3 SO 2 Cl / Pyridine (^) Compound B potassium t-butoxide DMF
Compound C
Compound D
OH CF 3 SO 2 Cl / Pyridine (^) Compound E potassium t-butoxide DMF
Compound F
Rate = 155 minutes
Rate = 5 minutes
5a. What is the structure for compound C? (2 points)
5b. What is the structure for compound F? (2 points)
5c. Explain why the rate for the two reactions are so different. Use energy diagrams to help answer the question. (7 points)
5d. If compound A or D are heated in the presence of 1M H 2 SO 4 , then two new major products (compounds G & H) are formed with the molecular formula C 10 H 20 O. These two molecules have very similar NMR spectra and very similar Rf values of each other; however, G & H are fairly different than compounds A or D. What are the structures of compounds G & H? (4 points)
5e. Choose one of the conversions and show a mechanism that accounts for the formation of either compound G or H from either compound A or D under 1M H 2 SO 4 reaction conditions. (8 points)
5f. Would you expect G & H to be the only products? Explain very briefly. (2 points)